Zelda reads all your letters but regrets that she cannot answer them all personally

Should I have an affair with my married boss?

I have fallen in love with the man I think I want to spend the rest of my life with – but it’s very complicated. First, he is married and, second, he is one of my bosses at work. It’s a big company so I don’t work directly for him. He is very flirtatious with me when no one is around and has suggested that we have dinner together. I am 31 and he is ten years older and has two children aged ten and eight. I feel guilty but I want to accept his invitation. What should I do?

Tempting as it may seem, your desire to be with this man is blinding you to the consequences. You say that you want to spend the rest of your life with him but, sadly for you, I expect that’s not his plan at all. Imagine for a moment how this might go. You have dinner, perhaps once, perhaps a few times and pretty soon it leads to sex. At first you love seeing him, the sex is fantastic and he tells you he adores you. It is exciting and lovely but because you think he is everything you need, settling for an affair becomes harder. The weekends and most evenings are lonely because he is with his wife and children. So you tell him you want to see more of him. He starts to feel under pressure to spend more time with you, so he withdraws a little and you start having rows. This situation might go on for a year or two, or even longer, until eventually he tells you that he can’t leave his wife and children. The truth suddenly hits you that this will never be more than an affair, leaving you heartbroken and realising that you have also missed some of your best child-bearing years. Added to this, you probably think that no one at work knows about the affair but you are, in fact, the hottest office gossip. And none of this even begins to take into account the hurt and devastation you would cause his wife and two children. So don’t pursue this relationship. Perhaps it would be best to look for a new job where you won’t be tempted by him, but make sure it is one you want.

He takes everything I say the wrong way

Some years ago a friend said I could rent his basement flat as I was struggling in an abusive relationship. However, he is a very anxious person who blames his overbearing mother for his chronic anxiety, so I have to walk on eggshells. Recently I upset him when I said, ‘Thank goodness for that,’ after he told me he was recovering from depression. Then, when I suggested that he should severely reprimand his solicitor for not progressing a conveyancing transaction, he went into decline and took to his bed, saying that I had made him feel like a little boy again. He is 65! I want to tell him to grow up but understand that it might be the worst thing to say. I am under such pressure tiptoeing around him, but I really can’t afford to move elsewhere.

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Perhaps saying ‘thank goodness’ was a little insensitive but, equally, it can be very frustrating and draining to be around someone who is constantly anxious and depressed. I suspect because, subconsciously, he associated your words with his overbearing mother, it brought back painful memories. He could not handle it because he has been so damaged. It’s difficult but you have to tread carefully because if he feels that he is being criticised in any way he is likely to relapse. You are right to say that telling him to grow up wouldn’t be a good idea, but you could gently explain to him that you don’t mean to upset him and suggest that perhaps his past experiences make him feel that he is being criticised when no criticism is intended. You can also encourage him to get help – it’s never too late. He could contact the mental health charity Mind (0300 123 3393, mind.org.uk) or see his GP for a referral to counselling. Try to make sure that you have an active and busy life of your own as well.

My partner is a secret cross-dresser

My partner and I are in our 70s and have been together for 20 years. Our relationship has always been strictly platonic – we are just very good friends. We have our own bedrooms and have been happy until recently, when I got a nasty shock. I discovered that he has a fetish for wearing women’s clothes. I am by no means a prude but this is something I have never experienced before. I desperately need advice on how to find counselling to help us get through this, as neither of us is computer literate and I feel isolated.

This is a shock for you, especially as you have been together for 20 years and your partner never had the courage to tell you. Though some men cross-dress for sexual pleasure or because they want to change sex, most do it because they feel relaxed when dressed as a woman. Some women can accept this in their partner and are even happy to go out with them when they are dressed up. Others find it hard to come to terms with and prefer it if the man does this privately. So talk to your partner about this, ask him to give you time to adjust to the situation and, if you decide that you want to stay together, try to agree on an arrangement that suits you both. For further support and advice, you should contact the Beaumont Society (01582 412220, beaumontsociety.org.uk). You could also try relationship counselling with Relate (0300 100 1234, relate.org.uk).

If you have a problem, write to Zelda West-Meads at: YOU, Northcliffe House, 2 Derry Street, London W8 5TS, or email z.west-meads@you.co.uk

Zelda reads all your letters but regrets that she cannot answer them all personally